diff --git a/matrix_puppeteer_line/portal.py b/matrix_puppeteer_line/portal.py
index 148ff00..aad7eff 100644
--- a/matrix_puppeteer_line/portal.py
+++ b/matrix_puppeteer_line/portal.py
@@ -18,6 +18,8 @@ import mimetypes
 import asyncio
 
 import magic
+from random import randint
+from os import remove
 
 from mautrix.appservice import AppService, IntentAPI
 from mautrix.bridge import BasePortal, NotificationDisabler
@@ -122,20 +124,25 @@ class Portal(DBPortal, BasePortal):
             return
         # TODO deduplication of outgoing messages
         text = message.body
-        media_id = None
-        if message.msgtype == MessageType.EMOTE:
-            text = f"/me {text}"
+        if message.msgtype.is_text:
+            if message.msgtype == MessageType.EMOTE:
+                text = f"/me {text}"
+            message_id = await sender.client.send(self.chat_id, text)
         elif message.msgtype.is_media:
-            # if message.file and decrypt_attachment:
-            #     data = await self.main_intent.download_media(message.file.url)
-            #     data = decrypt_attachment(data, message.file.key.key,
-            #                               message.file.hashes.get("sha256"), message.file.iv)
-            # else:
-            #     data = await self.main_intent.download_media(message.url)
-            # mime_type = message.info.mimetype or magic.from_buffer(data, mime=True)
-            # TODO media
-            return
-        message_id = await sender.client.send(self.chat_id, text)
+            if message.file and decrypt_attachment:
+                data = await self.main_intent.download_media(message.file.url)
+                data = decrypt_attachment(data, message.file.key.key,
+                                          message.file.hashes.get("sha256"), message.file.iv)
+            else:
+                data = await self.main_intent.download_media(message.url)
+            mime_type = message.info.mimetype or magic.from_buffer(data, mime=True)
+
+            # TODO Set path from config
+            file_path = f"/dev/shm/file_{randint(0,1000)}{mimetypes.guess_extension(mime_type)}"
+            temp_file = open(file_path, 'wb')
+            temp_file.write(data)
+            message_id = await sender.client.send_file(self.chat_id, file_path)
+            remove(file_path)
         # TODO Handle message-send timeouts better
         if message_id != -1:
             msg = DBMessage(mxid=event_id, mx_room=self.mxid, mid=message_id, chat_id=self.chat_id)
diff --git a/matrix_puppeteer_line/rpc/client.py b/matrix_puppeteer_line/rpc/client.py
index aa58f0c..eab9833 100644
--- a/matrix_puppeteer_line/rpc/client.py
+++ b/matrix_puppeteer_line/rpc/client.py
@@ -73,6 +73,10 @@ class Client(RPCClient):
         resp = await self.request("send", chat_id=chat_id, text=text)
         return resp["id"]
 
+    async def send_file(self, chat_id: int, file_path: str) -> int:
+        resp = await self.request("send_file", chat_id=chat_id, file_path=file_path)
+        return resp["id"]
+
     async def set_last_message_ids(self, msg_ids: Dict[int, int]) -> None:
         await self.request("set_last_message_ids", msg_ids=msg_ids)
 
diff --git a/puppet/src/client.js b/puppet/src/client.js
index b20223b..ba2f3e2 100644
--- a/puppet/src/client.js
+++ b/puppet/src/client.js
@@ -228,6 +228,7 @@ export default class Client {
 				login: req => this.puppet.waitForLogin(req.login_type, req.login_data),
 				cancel_login: () => this.puppet.cancelLogin(),
 				send: req => this.puppet.sendMessage(req.chat_id, req.text),
+				send_file: req => this.puppet.sendFile(req.chat_id, req.file_path),
 				set_last_message_ids: req => this.puppet.setLastMessageIDs(req.msg_ids),
 				get_chats: () => this.puppet.getRecentChats(),
 				get_chat: req => this.puppet.getChatInfo(req.chat_id),
diff --git a/puppet/src/puppet.js b/puppet/src/puppet.js
index 4fe83a1..9c53634 100644
--- a/puppet/src/puppet.js
+++ b/puppet/src/puppet.js
@@ -396,6 +396,36 @@ export default class MessagesPuppeteer {
 				imageUrl))
 	}
 
+	async sendFile(chatID, filePath) {
+		return { id: await this.taskQueue.push(() => this._sendFileUnsafe(chatID, filePath)) }
+	}
+
+	async _sendFileUnsafe(chatID, filePath) {
+		await this._switchChat(chatID)
+		const promise = this.page.evaluate(
+			() => window.__mautrixController.promiseOwnMessage())
+
+		// TODO Exit when the attach button is unclickable,
+		// 		like in chats with a bot
+		const [fileChooser] = await Promise.all([
+			this.page.waitForFileChooser(),
+			this.page.click("#_chat_room_plus_btn")
+		])
+		await fileChooser.accept([filePath])
+
+		// TODO Commonize with text message sending
+		try {
+			this.log("Waiting for message to be sent")
+			const id = await promise
+			this.log(`Successfully sent message ${id} to ${chatID}`)
+			return id
+		} catch (e) {
+			// TODO Handle a timeout better than this
+			this.error(`Timed out waiting for message to ${chatID}`)
+			return -1
+		}
+	}
+
 	async startObserving() {
 		this.log("Adding chat list observer")
 		await this.page.evaluate(